


A Night To Remember

by notinthisuniverse



Series: Homestuck Reader Inserts [4]
Category: Homestuck
Genre: F/M, Reader Insert, Smut
Language: English
Status: In-Progress
Published: 2014-04-02
Updated: 2014-04-02
Packaged: 2018-01-17 23:14:51
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,239
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1406191
Author URL: https://archiveofourown.org/users/notinthisuniverse/pseuds/notinthisuniverse
Summary: <blockquote class="userstuff">
            <p>It's your first date with Bro Strider and you are hella nervous...</p>
          </blockquote>





	1. Chapter 1

You’re arguing with your friend, at the moment. “I don’t want to go out! I’m fine (friend’s name)!” “You can’t spend another night in your pajamas watching movies and eating ice cream, Y/n!” You’re fine really, you’d just caught your last boyfriend cheating on you five months ago and then dumped him. Yep, you’re totally fine. “Come on, it’s been five months! You can’t just sit around here sulking! You have got to get out there! I’m not asking you to date again, just to get out and have fun,” your friend exclaims, crossing her arms. You roll your eyes, if you don’t say yes your friend won’t stop pestering you. 

“Fine,” you sigh, “I’ll go.” “Good,” she smiles, grabbing your arm, “now go get a shower and get ready, I’m dying to see that new club Skaia!” You roll your eyes again and sluggishly head to your bathroom. After showering, you go to your room and put on your short strapless red dress and do your hair and make-up. You then head to the living room where your friend is waiting. “Goddamn,” your friend gasps, “you’re gonna be the life of the party, (y/n)! You look amazing! You’ve got to see my dress though!” She removes her coat to show her short black dress with one sequined shoulder strap. You laugh, “You had this planned all along.” “Well yeah,” your friend says smirking and grabbing your elbow, “now come on, let’s go!”

You quickly grab your coat while your friend drags you to her car, barely giving you time to lock your door. You both get in her car, and your friend begins driving over to Skaia. The entire ride over she chats about how cool it’s supposed to be, meanwhile you roll your eyes and rest your head against the window until she parks the car, a few blocks away from Skaia. Once you get to the club, you pay and get into the club. “Geez,” you think once you get inside, “It sure is crowded here.” All of a sudden, your friend jumped up, excited about the song playing and running to the dance floor, leaving you alone.

You now have been sitting alone sulking and drinking some sort of alcoholic beverage for an hour now, meanwhile your friend is out on the dance floor somewhere. You sigh, looking around for her on the dance floor. All of a sudden, your eyes land upon this gorgeous man. He’s dancing by himself, his movements smooth and fluid. All eyes are on him, and he doesn’t even seem to notice. Maybe he has noticed, and was just used to it or simply doesn’t care. 

Either way, he’s quite a sight. He’s wearing a plain outfit: black baseball cap with white blonde hair peeking out the back of it, tight fitting white t-shirt, dark blue jeans, black sneakers (yeah right, like you actually know what brand it is, the dance floor is so crowded you can barely see them) and the most unique pair of sunglasses you have ever seen. “God damn,” you think to yourself, “he’s practically oozing confidence. He’s gorgeous, and he knows it. If I would have known I’d see such a magnificent looking man, I would have gone with (friend’s name) without arguing with her so much.”

You sigh and turn to your drink, stirring it with your straw, there’s no way he would notice you. “Unless,” you consider, “I go out and make him notice me.” If he can go out there and dance without a care in the world, then you sure as hell can too! You nervously swallow the rest of your drink, and head out onto the dance floor. You walk right past him, flipping your hair and not making eye contact, and start dancing a little ways away from him. You glance at him out of the corner of your eye, and see what appears to be him looking in your direction. You smirk, a bit shocked that he’s paying attention to you. Either way, you’re having a great time dancing. You haven’t even thought about your stupid, cheating ex! You grin, lost in your thoughts, when you feel a hand tapping your shoulder. You turn around to see the attractive blonde with the shades. “Care to dance,” he says coolly. “Sure,” you reply as the song changed. “Damn, that was smooth,” you mutter quietly.

“I’m Dirk, most people call me Bro.” “Most people call me (Y/n).” “Two could play it this game,” you think confidently, “I can be just as cool as he is.” You both continue to dance for a while before he grabs your hand and pulls you off the dance floor to an empty table. You sit down, confused by the suddenness of his actions. “I like you, y/n. Mind telling me about yourself,” he shouts over the music as he sits down. You begin telling him your interests, while he simply nods every once in a while. “What about you?” He tells you about “cool and ironic” Smuppets and about his passion for rapping. He keeps bringing up someone or something called Lil Cal, which you’re pretty sure is a puppet too. 

“It’s fascinating, hearing him talk about his passions, no matter how calm and cool he’s acting,” you ponder, “It’s obvious he’s really passionate about them.” You smile and rest your hand on his, right as your friend stumbles over, obviously drunk. “Hey (y/n), I see you met someone,” she says as she turns to look at Bro. “I was gonna head back,” she states, leaning on you a bit. “I got a cab,” she says, handing you her keys, “so you gotta keep an eye on my car.” “Okay,” you nod, taking her keys and putting them in your coat pocket. You watch as (friend’s name) walks away, exiting the club, leaving you alone with Bro. “So, it’s kinda late,” Bro states, looking at his phone. “So it is.” “Wanna come to my place,” he says coolly, “I’d like to get to know you more.” “Sure,” you reply, putting your coat on and walking to your friend’s car, leaving Bro Strider to catch up with you. 

The car ride is a quiet one, as the only talking is from Bro giving you instructions to his apartment. You can’t help but anticipate what could happen when you’re alone with this gorgeous man. You blush and grin in anticipation as he directs you to the parking lot of his apartment complex. You park the car and get out, waiting for Bro to give you further instructions on where his apartment is. “You coming,” Bro questions, seeing as he’s at the door to the building. “Sorry, I must have zoned out,” you say while locking the car. You quickly walk inside to see Bro keeping the door of an elevator open and speed walk inside. You tap your foot nervously, as the elevator takes you closer to Bro’s apartment. The elevator dings, pulling you from your thoughts. “Something bothering you,” Bro asks. “Nope,” you lie. “Smooth (y/n),” you congratulate yourself mentally, still following Bro to his apartment. You shift around nervously as he opens the door. 

“Ladies first.” You walk into the apartment and look around. “Quite a nice place you’ve got here,” you tell Bro. “Thanks.” You see a bunch of puppets, practically on every surface of the apartment. “Those must be smuppets,” you think. “You want something to drink,” Bro asks from the kitchen. “Uh no thanks, I’m alright.” He returns from the kitchen with a glass of what looks like apple juice before moving some smuppets over and sitting down on the couch. “Sit down (y/n), I don’t bite.” You sit down next to him. “So, now that we don’t have to shout to hear each other, tell me more about yourself.” You blush, and start answering the multitude of questions from him. After talking to him for about an hour, you see him staring at you intently.

“Uh Bro? You okay?” You lean over to face him. “Yeah fine. I just wanted to try something.” “Alright, go crazy I guess.” He leans over and kisses you, cupping your face with one hand gently. You kiss back, moving one of your hands to his hip and other to the back of his neck. He removes his hat and you entwine your fingers in his white blonde hair as you two begin making out. Before you know it, he’s pulling away from the kiss and taking off his shirt. “This okay?” “It’s uh f-fine with me,” you stutter. You go back to kissing and you grab his hips tugging him closer to you. He smirks and moves his hand to your hair, coiling some of it around his fingers. He bites your lip playfully, and you both begin french kissing. You explore his mouth teasingly before he stops kissing you and begins nipping teasingly at your neck. He stops at your collar bone once he hears your gasp softly and begins to bite and kiss at that spot repeatedly, insistent on leaving his mark. 

You feel his hands go to your shoulders, as he removes your coat, smirking slyly. “So, my room?” You nod and take his hand, letting him lead the way to his room. Once there, you sit on his bed. Bro sits next to you and you begin nibbling on his jawline softly, getting payback for the hickey you know is going to be on your neck and collarbones tomorrow. You feel his hands go to the back of your dress as he unzips it, and you stand, letting the dress pool around your ankles. Stepping out of the dress, you lean over and unzip his jeans, “It’s not fair that I’m only in my undies and you’re still mostly dressed.” “Fair enough,” Bro replies, standing up and taking off his jeans and tossing them on the floor. Pushing him onto the bed, you begin kissing again as he unhooks the strapless bra you’re wearing and throws it to some random corner of his room. He flips you over so he’s on top and lays in between your legs and your hand finds its way to his plush rump. 

You hook your fingers into the sides of his boxers and tug them off, and Bro stands up, sliding them off his well-toned body. You gaze at him as he goes to the drawer next to his bed and pulls out lube and a condom and sets it down at the edge of bed. He then pulls you up and slips your panties off onto the floor before getting back on the bed and pulling you on top of him. He trails his lips all over your body, making sure to leave a few love bites along the way, before stopping at your core. He grabbed the lube and carefully lubed up two of his fingers before pushing you back down onto the bed. He spreads your legs, and slips a finger inside of you. He begins moving his finger slowly at first, but then begins pumping it back and forth after hearing a breathy moan from you. He added another finger, enjoying the needy gasps and moans he’s hearing. He curls his fingers, looking for your g-spot, smiling when he hears your pleasured groans. He fells you clench around his fingers and removes his hand before leaning over you, in between your legs. “He’s hard,” you realize, feeling his dick against your thigh. You grab the condom and unwrap the foil, before placing the rubber at his tip and covering his entire length. He opens the bottle of lube and lubes himself up. He tosses the bottle on the floor somewhere and lines himself up with your entrance. 

“Ready?” You nod, “Yup.” You feel him grab your hips and enter you. He hesitates a minute before thrusting into you repeatedly. Your hips jerk up to meet his thrusts, as Bro grunts and moans huskily. You moan as he hits your g-spot, and he begins to thrust against it. “F-faster dammit,” you gasp. He complies with your wishes and his hips stutter as he thrusts faster. You’re close, and Bro seems to know it as he moves a hand to play with your clit. That drove you over the edge, and you came, your walls clenching against Bro. He came in a few more thrusts, before resting his forehead against yours and kissing you chastely. Bro then pulled out, threw the condom out, and grabbed his shirt off the floor and handed it to you to wear. You smiled as he got under the covers and put his shirt on. Bro gestured for you to get in bed with him and you got under the covers, allowing Bro to wrap an arm around your waist as the two of you drifted off to sleep.

You wake up in the morning, a bit disoriented. “Wait a minute,” you ponder, “this isn’t my apartment.” You look down to see you’re in a man’s white t-shirt and then roll over to see a naked Bro Strider, asleep, with the sheet covering part of his well-toned torso and lower half. You recall last night’s events and grin, chuckling to yourself. Bro groggily turns to you, and smiles. “So, wanna go on an actual date?” You grin, “What do you think?”


	2. A Date to Remember

**Summary for the Chapter:**

> It's your first date with Bro Strider and you are hella nervous...

It had been a week since your rendezvous with the one and only Bro Strider, and you were both finally going on a real date. (Not that you didn’t enjoy yourself the first time you were with him, of course.) You had just gotten out of the shower and were trying to figure out what to wear. It was your first date after all, so you had to wear something casual. You sighed as you rummaged through your closet. “Just great, all my clothes look like crap. I would feel like this today of all days,” you grumbled. 

You decided to settle for a (f/c) shirt, blue jeans and boots. “Well, I do look pretty good,” you thought to yourself before heading into your bathroom to put makeup on. Just as you finish putting on mascara, you hear the doorbell ring. “Shit,” you exclaim, running to the door and opening it hurriedly. “Bro,” you say, trying to sound cool. “Y/n. You look nice.” “Thanks,” you smile, tucking a piece of your hair behind your ear, trying to hide your blush. “Ready to go?” You snapped out of your train of thought quickly, “Oh uh yeah.” You grab your purse and keys, locking the door to your apartment behind you before following Bro to the elevator. 

“You coming,” Bro asks, smirking, his arm blocking the elevator door from closing. You nod and run into the elevator and stand next to Bro, trying to hide your nervousness and play it cool as the elevator doors close. “How have you been,” Bro asks coolly as the elevator begins to descend. “I’ve been good, and yourself?” “I’ve been great, especially after meeting you,” he says boldly. You blush, “g-great.” “Nice one (y/n),” you think to yourself. He grabs your hand as the elevator doors open and leads you to his car, opening the passenger door for you. You get in the car, wondering where Bro could be taking you. He got in the car and started it up. “So where are we going Bro?” “It’s a surprise (y/n),” Bro said chuckling to himself. 

After a while of driving, you pull up in front of a small café. “I was hoping we could go somewhere quiet where we could get to know each other better.” “Uh I’m cool with that.” You exit the car and head into the café with Bro. You follow him to the cashier. “I’ll have a medium coffee. Black. (Y/n), what are you having?” “I’ll uh have the same thank you.” Bro paid the woman began to lead you to a booth in a private corner of the café. “You going to sit down,” Bro asked, noticing you were staring off into space. “Oh uh shit sorry Bro,” you blushed, sitting down across from him. “Dammit, this is the second time this has happened,” you thought irritated. “How have you been Bro?” “I’ve been good…I’ve been doing better though since I’ve met you,” he said, pulling down his shades and winking at you before quickly pulling his shades over his eyes again. “So tell me more about yourself, (y/n).” 

You began to tell him about your life. You told him about your friends, your job, your siblings (or lack thereof, if you are an only child), your apartment, anything you could think of. You learned a lot about Bro too. You learned that he actually was a DJ at that club Sburb, that he had a younger brother named Dave, and much more. Bro also learned a lot about you, but that’s beside the point. “I’m glad you agreed to go on a date with me, (y/n),” he stated coolly. You noticed the tips of his ears and cheeks were flushed red. So the famous Bro Strider was blushing, over you of all people! “I’m glad I did too, Bro. I’m hoping I get to have a second date with you.” “Oh you will,” he said smirking. You took the opportunity to cup his cheeks and pull him in for a kiss, which soon turned into a passionate make out session. Bro licked your bottom lip sensually, asking for permission, which you gave him, and he began to explore the familiar territory. 

One of his hands moved from your hips to your hair as he gripped it, pulling away from you as the waitress sets your coffee down. “Damn,” you accidentally say out loud, unhappy you were interrupted by the waitress bringing you your coffee. Bro smirked, “disappointed? We can kiss later you know.” “Shit uh sorry…you weren’t supposed to hear that,” you say blushing again. “I must be as read as a tomato,” you sigh, deep in thought. “You have a lot on your mind,” Bro says, taking a sip of his coffee. “Mostly you,” you giggle to yourself. “What’s so funny,” Bro asks. “Uh just thinking is all,” you sip at your coffee, “nothing special.” Bro leaned closer. “You have a cute laugh by the way.” “You really like making me blush don’t you?” “Maybe,” he said smirking. “You know,” you said playfully, “you have a cute blush.” “I do not blush.” You took out your mirror and lifted it up to Bro’s face. “That looks like a blush to me,” you smirked at him. “I guess you caught me. I’m blushing because of you. Something I rarely do (y/n).” Your blush returned suddenly as he grabbed your hand softly and rested his other hand on top of it. 

“I’m having a great time with you (y/n). What are you doing tomorrow?” “Nothing why?” “Wanna come back to my apartment?” “Bro,” you laughed, playfully shoving him. “What? Just a question.” “Sure,” you smiled. I’d love to come to your apartment. As you both finished your coffee, he grabbed your hand and pulled you to his car. Even if this wasn’t anything like your last time at his place, it was something you were definitely looking forward to.

**Notes for the Chapter:**

> Part 2! Hope you like it!

**Author's Note:**

> You've been laying low for a while...you caught your last boyfriend cheating on you and began to stay in. But tonight, your friend is dragging you out to a club, and you meet the one, the only Bro Strider. Anything could happen. ;3


End file.
